IE60073B1 - New peptide derivatives having a polycyclic nitrogenous structure, process for the preparation thereof and pharmaceutical compositions containing them - Google Patents

New peptide derivatives having a polycyclic nitrogenous structure, process for the preparation thereof and pharmaceutical compositions containing them

Info

Publication number: IE60073B1
Authority: IE; Ireland
Prior art keywords: arg; formula; lys; pharmaceutically acceptable; cyclo
Prior art date: 1987-02-13

Application number

IE38288A

Other languages

English (en)

Other versions

IE880382L (en

Inventor

Michel Vincent

Claude Cudennec

Georges Remond

Original Assignee

Adir

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-02-13

Filing date

1988-02-12

Publication date

1994-06-01

1988-02-12 Application filed by Adir filed Critical Adir

1988-08-13 Publication of IE880382L publication Critical patent/IE880382L/xx

1994-06-01 Publication of IE60073B1 publication Critical patent/IE60073B1/en

Links

238000000034 method Methods 0.000 title claims description 19
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 6
230000008569 process Effects 0.000 title claims description 4
108090000765 processed proteins & peptides Proteins 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 46
150000003839 salts Chemical class 0.000 claims abstract description 19
239000002253 acid Substances 0.000 claims abstract description 18
-1 alkyl radical Chemical class 0.000 claims abstract description 17
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 50
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 22
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
239000004472 Lysine Substances 0.000 claims description 4
PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 claims description 3
230000009471 action Effects 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
CKGCFBNYQJDIGS-LBPRGKRZSA-N (2s)-2-azaniumyl-6-(phenylmethoxycarbonylamino)hexanoate Chemical compound [O-]C(=O)[C@@H]([NH3+])CCCCNC(=O)OCC1=CC=CC=C1 CKGCFBNYQJDIGS-LBPRGKRZSA-N 0.000 claims description 2
ADKDJHASTPQGEO-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[b]pyrrole Chemical compound C1CNC2CCCC21 ADKDJHASTPQGEO-UHFFFAOYSA-N 0.000 claims description 2
NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 claims description 2
POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 claims description 2
ODSNARDHJFFSRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical compound C1CCCC2CNCC21 ODSNARDHJFFSRH-UHFFFAOYSA-N 0.000 claims description 2
CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 claims description 2
GYLMCBOAXJVARF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptane Chemical compound C1C2CCC1NC2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 claims description 2
KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical compound C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 claims description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
230000009467 reduction Effects 0.000 claims description 2
ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-OUBTZVSYSA-N Ammonia-15N Chemical group [15NH3] QGZKDVFQNNGYKY-OUBTZVSYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
FAJFGLZHUIUNSS-NSHDSACASA-N benzyl (2s)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoate Chemical compound [O-][N+](=O)NC(N)=NCCC[C@H](N)C(=O)OCC1=CC=CC=C1 FAJFGLZHUIUNSS-NSHDSACASA-N 0.000 claims 1
125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
150000005840 aryl radicals Chemical class 0.000 abstract 1
229940126601 medicinal product Drugs 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
125000004434 sulfur atom Chemical group 0.000 abstract 1
125000001544 thienyl group Chemical group 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 18
241001465754 Metazoa Species 0.000 description 12
230000003595 spectral effect Effects 0.000 description 10
241000699670 Mus sp. Species 0.000 description 9
230000005875 antibody response Effects 0.000 description 9
230000000694 effects Effects 0.000 description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
238000004949 mass spectrometry Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
241001494479 Pecora Species 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 5
239000002585 base Substances 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
206010057249 Phagocytosis Diseases 0.000 description 4
201000001441 melanoma Diseases 0.000 description 4
230000008782 phagocytosis Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
208000006313 Delayed Hypersensitivity Diseases 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
239000011651 chromium Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241000588747 Klebsiella pneumoniae Species 0.000 description 2
MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 description 2
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
150000001793 charged compounds Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
YQGDEPYYFWUPGO-UHFFFAOYSA-N gamma-amino-beta-hydroxybutyric acid Chemical compound [NH3+]CC(O)CC([O-])=O YQGDEPYYFWUPGO-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
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238000007912 intraperitoneal administration Methods 0.000 description 2
238000001471 micro-filtration Methods 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
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WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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IESDGNYHXIOKRW-YXMSTPNBSA-N (2s)-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s,3r)-2-amino-3-hydroxybutanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(O)=O IESDGNYHXIOKRW-YXMSTPNBSA-N 0.000 description 1
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JXJYTERRLRAUSF-CVEARBPZSA-N (2s,3r)-2-hydroxy-4-phenyl-3-(phenylmethoxycarbonylamino)butanoic acid Chemical compound C([C@H]([C@H](O)C(O)=O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 JXJYTERRLRAUSF-CVEARBPZSA-N 0.000 description 1
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238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
WSMBEQKQQASPPL-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole-1-carboxylic acid Chemical compound C1CCCC2C(C(=O)O)NCC21 WSMBEQKQQASPPL-UHFFFAOYSA-N 0.000 description 1
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000008512 biological response Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
238000000684 flow cytometry Methods 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
230000002519 immonomodulatory effect Effects 0.000 description 1
230000028993 immune response Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000009545 invasion Effects 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
210000000822 natural killer cell Anatomy 0.000 description 1
230000031942 natural killer cell mediated cytotoxicity Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000008213 purified water Substances 0.000 description 1
DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
DFVFTMTWCUHJBL-BQBZGAKWSA-N statine Chemical compound CC(C)C[C@H](N)[C@@H](O)CC(O)=O DFVFTMTWCUHJBL-BQBZGAKWSA-N 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000001173 tumoral effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Immunology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Saccharide Compounds (AREA)
Financial Or Insurance-Related Operations Such As Payment And Settlement (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

IE38288A 1987-02-13 1988-02-12 New peptide derivatives having a polycyclic nitrogenous structure, process for the preparation thereof and pharmaceutical compositions containing them IE60073B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8701810A FR2610934B1 (fr)	1987-02-13	1987-02-13	Nouveaux derives peptidiques a structure polycyclique azotee, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (2)

Publication Number	Publication Date
IE880382L IE880382L (en)	1988-08-13
IE60073B1 true IE60073B1 (en)	1994-06-01

Family

ID=9347880

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE38288A IE60073B1 (en)	1987-02-13	1988-02-12	New peptide derivatives having a polycyclic nitrogenous structure, process for the preparation thereof and pharmaceutical compositions containing them

Country Status (16)

Country	Link
US (1)	US4965250A (de)
EP (1)	EP0282374B1 (de)
JP (1)	JPH0649718B2 (de)
AT (1)	ATE63125T1 (de)
AU (1)	AU604090B2 (de)
CA (1)	CA1331672C (de)
DE (1)	DE3862596D1 (de)
DK (1)	DK74988A (de)
ES (1)	ES2006076A6 (de)
FR (1)	FR2610934B1 (de)
GR (1)	GR1000079B (de)
IE (1)	IE60073B1 (de)
NZ (1)	NZ223509A (de)
OA (1)	OA08715A (de)
PT (1)	PT86755B (de)
ZA (1)	ZA88995B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2616663B1 (fr) *	1987-06-16	1989-08-18	Adir	Nouveaux tripeptides a structure polycyclique azotee, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CA1340588C (en) *	1988-06-13	1999-06-08	Balraj Krishan Handa	Amino acid derivatives
GB8927913D0 (en) *	1989-12-11	1990-02-14	Hoffmann La Roche	Amino acid derivatives
FR2663336B1 (fr) *	1990-06-18	1992-09-04	Adir	Nouveaux derives peptidiques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
US6177405B1 (en) *	1992-07-22	2001-01-23	Kenji Nishioka	Cyclic analogs of tuftsin
DE69410881T2 (de) *	1993-03-22	1999-02-11	Leonida Dr. Roma Grippa	Monoessigsäure Derivate der Peptide leu-phe-ala und ala-leu-phe und deren Verwendung in der Erkennung und Vernichtung von Tumorzellen und virusinfizierten Zellen
US5569745A (en) *	1994-02-25	1996-10-29	Resolution Pharmaceuticals Inc.	Peptide-Chelator conjugates
US5662885A (en) *	1994-07-22	1997-09-02	Resolution Pharmaceuticals Inc.	Peptide derived radionuclide chelators
US6159748A (en) *	1995-03-13	2000-12-12	Affinitech, Ltd	Evaluation of autoimmune diseases using a multiple parameter latex bead suspension and flow cytometry
EP0837875A4 (de) *	1995-03-29	1998-10-07	Merck & Co Inc	Inhibitoren der farnesyl-proteintransferase
WO1998018763A1 (en) *	1996-10-25	1998-05-07	Tanabe Seiyaku Co., Ltd.	Tetrahydroisoquinoline derivatives
CN102099035A (zh)	2008-05-16	2011-06-15	诺瓦提斯公司	Iap抑制剂的免疫调节

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2343034C2 (de) *	1973-08-25	1984-08-23	Hoechst Ag, 6230 Frankfurt	Tetrapeptide mit phagocytose-stimulierender Wirkung, Verfahren zu deren Herstellung und deren Verwendung
CH611878A5 (de) *	1974-07-04	1979-06-29	Takeda Chemical Industries Ltd
IT8021120A0 (it) *	1979-04-02	1980-04-01	Inst Organicheskogo Sinteza Ak	Analogo ciclico del peptide naturale stimolante la fagocitosi: treonile-ciclo (n-lisile-prolile-arginile).
FR2575753B1 (fr) *	1985-01-07	1987-02-20	Adir	Nouveaux derives peptidiques a structure polycyclique azotee, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

1987
- 1987-02-13 FR FR8701810A patent/FR2610934B1/fr not_active Expired
1988
- 1988-01-25 US US07/148,027 patent/US4965250A/en not_active Expired - Fee Related
- 1988-01-25 CA CA000557303A patent/CA1331672C/fr not_active Expired - Fee Related
- 1988-02-10 OA OA59283A patent/OA08715A/xx unknown
- 1988-02-12 DK DK074988A patent/DK74988A/da not_active Application Discontinuation
- 1988-02-12 AU AU11669/88A patent/AU604090B2/en not_active Ceased
- 1988-02-12 ZA ZA880995A patent/ZA88995B/xx unknown
- 1988-02-12 PT PT86755A patent/PT86755B/pt not_active IP Right Cessation
- 1988-02-12 ES ES8800386A patent/ES2006076A6/es not_active Expired
- 1988-02-12 IE IE38288A patent/IE60073B1/en not_active IP Right Cessation
- 1988-02-12 DE DE8888400315T patent/DE3862596D1/de not_active Expired - Lifetime
- 1988-02-12 GR GR880100079A patent/GR1000079B/el unknown
- 1988-02-12 EP EP19880400315 patent/EP0282374B1/de not_active Expired - Lifetime
- 1988-02-12 AT AT88400315T patent/ATE63125T1/de not_active IP Right Cessation
- 1988-02-12 NZ NZ223509A patent/NZ223509A/en unknown
- 1988-02-12 JP JP63030709A patent/JPH0649718B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US4965250A (en)	1990-10-23
AU1166988A (en)	1988-08-18
IE880382L (en)	1988-08-13
GR880100079A (en)	1988-12-16
DE3862596D1 (de)	1991-06-06
GR1000079B (el)	1990-11-29
PT86755A (pt)	1988-03-01
FR2610934B1 (fr)	1989-05-05
DK74988A (da)	1988-08-14
ZA88995B (en)	1988-08-10
NZ223509A (en)	1990-11-27
PT86755B (pt)	1992-05-29
EP0282374B1 (de)	1991-05-02
JPH0649718B2 (ja)	1994-06-29
FR2610934A1 (fr)	1988-08-19
CA1331672C (fr)	1994-08-23
JPS63203698A (ja)	1988-08-23
ATE63125T1 (de)	1991-05-15
OA08715A (fr)	1989-03-31
AU604090B2 (en)	1990-12-06
EP0282374A1 (de)	1988-09-14
DK74988D0 (da)	1988-02-12
ES2006076A6 (es)	1989-04-01

Legal Events

Date	Code	Title	Description
1997-11-05	MM4A	Patent lapsed

Publication	Publication Date	Title
US4720484A (en)	1988-01-19	Peptide compounds having a nitrogenous polycyclic structure
US5317014A (en)	1994-05-31	Peptides and pseudopeptides derived from tachykinin
AU625456B2 (en)	1992-07-09	Diol-containing renin inhibitors
IE60073B1 (en)	1994-06-01	New peptide derivatives having a polycyclic nitrogenous structure, process for the preparation thereof and pharmaceutical compositions containing them
AU2014392A (en)	1992-11-02	Anti-thrombotic peptides and pseudopeptides
NZ199310A (en)	1985-10-11	Peptides and peptide derivatives containing 3-5 amino acid residues;compositions
US4362716A (en)	1982-12-07	Dipeptides, their preparation and compositions containing them
US4346104A (en)	1982-08-24	Novel substituted phenylacetic acid amide compounds
US4250192A (en)	1981-02-10	Novel substituted phenylacetic acid amide compounds
US5047400A (en)	1991-09-10	Tripeptide compounds having a nitrogenous polycyclic structure
US4421765A (en)	1983-12-20	Substituted phenylacetic acid amide compounds
HU185229B (en)	1984-12-28	Process for preparing pharmaceutically active peptides and acetates thereof
US5494898A (en)	1996-02-27	Peptide skeletal muscle relaxants
US4247543A (en)	1981-01-27	Organic compounds
IE900850L (en)	1990-09-11	Sdk peptides, a preparation process of the same and¹therapeutic compositions containing them
CA2054651A1 (en)	1992-08-14	Peptide amides and amide dimers
US5108990A (en)	1992-04-28	Glutamic acid derivatives